2,2’-联噻吩-5-硼酸 | 132898-95-4

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 中文名称: 2,2’-联噻吩-5-硼酸
• 中文别名: 2,2'-联噻吩-5-硼酸；2,2'-双噻吩-5-硼酸；2,2-Bi噻吩-5-硼酸
• 英文名称: 2,2'-bithiophene-5-boronic acid
• 英文别名: (2,2'-bithiophen)-5-ylboronic acid；(5-thiophen-2-ylthiophen-2-yl)boronic acid
• CAS: 132898-95-4
• 化学式: C₈H₇BO₂S₂
• mdl: MFCD03086112
• 分子量: 210.085
• InChiKey: PPHSULIZZOEBDD-UHFFFAOYSA-N

物化性质

• 熔点：
  163-165℃

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96.9
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R22,R36/37/38
• 安全说明：
  S26,S37/39
• 危险性防范说明：
  P261,P264,P270,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P330,P362,P403+P233,P501
• 危险性描述：
  H302,H312,H332
• 储存条件：
  -20°C下保存，需避光并置于惰性气体环境中。

SDS

Name:	2 2 -Bithiophene-5-boronic acid 97% Material Safety Data Sheet
Synonym:
CAS:	132898-95-4

Section 1 - Chemical Product MSDS Name:2 2 -Bithiophene-5-boronic acid 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
132898-95-4	2,2'-Bithiophene-5-boronic acid	97%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.Moisture sensitive.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use foam, dry chemical, or carbon dioxide.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Store under nitrogen.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 132898-95-4: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: blue
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 127 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C8H7BO2S2
Molecular Weight: 210.08

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials, exposure to moist air or water.
Incompatibilities with Other Materials:
Strong oxidizing agents, bases, reducing agents, halogens, halogenated agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of sulfur, carbon dioxide, acrid smoke and fumes, oxides of boron.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 132898-95-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2,2'-Bithiophene-5-boronic acid - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 132898-95-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 132898-95-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 132898-95-4 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2,2’-联噻吩-5-硼酸 在 四(三苯基膦)钯 、 正丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 25.0h， 生成 4-[5-[5-bis[2,6-dimethyl-4-(2,3,4,5,6-pentafluorophenyl)phenyl]boranylthiophen-2-yl]thiophen-2-yl]-N,N-diphenylaniline
  参考文献：
  名称：

  D–π–A三芳基硼化合物具有可变的推挽特性，可通过修饰供体和受体部分实现

  摘要：

  一系列供体-联苯基-受体化合物的推挽特性已通过采用三苯胺或1,1,7,7-四甲基甲氧萘啶作为供体和B（2,6-Me 2-4 -RC 6 H 2来调节）2（R = Me，C 6 F 5或3,5-（CF 3）2 C 6 H 3）或B [2,4,6-（CF 3）3 C 6 H 2 ] 2作为受体。Ir催化的CH硼化用于硼基受体和四甲基甲氧戊啶供体的衍生中。通过电化学和光物理测量来评估供体和受体的强度。在溶液中，具有最强受体B [2,4,6-（CF 3）3 C 6 H 2 ] 2（（FMes）2 B）的化合物具有强烈的猝灭发射，而所有其他化合物均显示出有效的绿色至红（Φ ˚F = 0.80-1.00）或近红外（NIR; Φ ˚F= 0.27–0.48）的发射，具体取决于溶剂。值得注意的是，这项研究提出了三配位硼化合物有效发射NIR的第一个例子。观察到某些衍生物的高效固态红色发射，并且研究了有趣的聚集诱导的（FMes）2

  DOI：

  10.1002/chem.201405621
• 作为产物：
  描述：

  2,2'-联二噻吩 在 正丁基锂 、 硼酸三丁酯 、 sodium hydroxide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 生成 2,2’-联噻吩-5-硼酸
  参考文献：
  名称：

  Using the nitro group to induce π-stacking in terthiophenes

  摘要：

  介绍了单硝化低聚噻吩的新合成路线，以及其卤代衍生物（Br、I）的制备方法。在 DFT 计算的帮助下，观察到了一种不寻常的深红色，并解释了这种深红色是由于分子结构中存在大量的醌基。文中展示了 H(C4H2S)3NO2 和 Br(C4H2S)3NO2 这两种化合物的晶体结构。这两种化合物都具有通过分子间短接触（氢键以及后者的 NO2-Br 相互作用）固定在一起的平面片层；片层并不直接叠加，因此π堆叠的效果并没有最大化。此外，还介绍了这些材料的固态荧光和扩展胡克尔带状结构计算结果。

  DOI：

  10.1139/v09-165

文献信息

• Spectroelectrochemistry of alternating ambipolar copolymers of 4,4′- and 2,2′-bipyridine isomers and quaterthiophene
  作者：Pawel Zassowski、Sylwia Golba、Lukasz Skorka、Grazyna Szafraniec-Gorol、Marek Matussek、Dawid Zych、Witold Danikiewicz、Stanislaw Krompiec、Mieczyslaw Lapkowski、Aneta Slodek、Wojciech Domagala

  DOI：10.1016/j.electacta.2017.01.076

  日期：2017.3

  First report of π-conjugated push-pull copolymer systems with 4,4′-bipyridine moieties in the main macromolecular chain is presented. C-substitution pattern of electropolymerisable bithiophene pendants at the 4,4′-bipyridine unit offered the versatility to retain the latter as free amine, or convert it into bipyridylium salt. Both structures have been prepared and investigated, delivering the first

  首次报道了在大分子主链上具有4,4'-联吡啶部分的π-共轭推挽共聚物体系。在4,4'-联吡啶单元上的可电聚合联噻吩侧基的C取代模式提供了多功能性，可将后者保留为游离胺，或将其转化为联吡啶鎓盐。两种结构均已制备和研究，提供了具有构成扩展π键的紫精单元的聚合物的第一个实例。对这些新的聚合物体系及其2,2'-联吡啶类似物的详细电化学，光谱电化学和量子化学研究表明，尽管后者的线性结构和扩展的共轭有助于其适应重掺杂聚噻吩的特征性载流子，但共轭断裂通过跨4的元替换模式 4'-吡啶基单元使聚合物的行为像较短的低聚物链段的集合，具有更好的定义的电子跃迁和更清晰，更快的电致变色响应。观察到α，ω-双（2-吡啶基）四噻吩重复单元之间的有效π-π链间偶联，而在线性2,2'-联吡啶基聚合物中发现分子内相互作用占主导。尽管甲基紫精的联噻吩衍生物比其相应的非季铵化衍生物更不易电聚合，但所得的聚合物薄膜在进行后续的p和
• Syntheses and properties of thienyl-substituted dithienophenazines
  作者：Annemarie Meyer、Eva Sigmund、Friedhelm Luppertz、Gregor Schnakenburg、Immanuel Gadaczek、Thomas Bredow、Stefan-S Jester、Sigurd Höger

  DOI：10.3762/bjoc.6.135

  日期：——

  A series of dithienophenazines with different lengths of the oligomeric thiophene units (quaterthiophenes and sexithiophenes) was synthesized. The thiophene and phenazine units act as electron donors and acceptors, respectively, resulting in characteristic absorption spectra. The optical spectra were calculated using time-dependent density functional theory at the B3LYP/TZVP level and verify the experimental data. Adsorption of the dithienophenazines on highly ordered pyrolytic graphite (HOPG) was investigated by scanning tunneling microscopy, showing that one of the compounds forms highly organized self-assembled monolayers.

  一系列具有不同寡聚噻吩单元长度（四噻吩和六噻吩）的二噻吩并联化合物被合成。噻吩和苝嗪单元分别作为电子给体和受体，导致特征吸收光谱。利用B3LYP/TZVP水平的时变密度泛函理论计算了光谱，并验证了实验数据。利用扫描隧道显微镜研究了二噻吩并联化合物在高度有序的热解石墨（HOPG）上的吸附，结果显示其中一种化合物形成高度有序的自组装单分子层。
• Synthesis and spectroscopic studies of highly fluorescent, solvatochromic diastereomers with differentially stacked bithiophene-substituted quinoxaline rings
  作者：Ryan A. Ciufo、John J. Kreinbihl、Sarah R. Johnson、Jocelyn M. Nadeau

  DOI：10.1016/j.tet.2016.11.044

  日期：2017.1

  Diastereomeric C-shaped molecules containing closely stacked bithiophene-substituted quinoxaline rings were synthesized and characterized by NMR, UV–vis absorption, and fluorescence spectroscopy. The unique geometry of each diastereomer resulted in different degrees of π-overlap between the bithiophene-substituted quinoxaline ring chromophores, modulating their spectroscopic properties. The donor-acceptor nature

  合成了包含紧密堆积的联噻吩取代的喹喔啉环的非对映体C形分子，并通过NMR，UV-vis吸收和荧光光谱进行了表征。每个非对映异构体的独特几何结构导致联噻吩取代的喹喔啉环生色团之间的π重叠程度不同，从而调节了它们的光谱性质。该生色团的供体-受体性质导致其正溶剂化变色。1 H NMR和UV-vis吸收光谱证实π-π相互作用的存在，在这两种分子的喹喔啉环仅在之间，而是在噻吩环之间的基态顺异构体。与未堆叠发色团的化合物相比，它们显示出显着的最大发射红移，强正正溶剂变色，增加的谱带展宽和更大的斯托克斯位移。此外，该顺式异构体一致显示λ max时，EM看重红移和较大的带变宽和斯托克斯位移相比，抗由于更大的π重叠异构体顺式异构体。
• The role of borole in a fully conjugated electron-rich system
  作者：Sanghoon Kim、Kee-hyung Song、Sang Ook Kang、Jaejung Ko

  DOI：10.1039/b312028g

  日期：——

  The reaction of the 3,3′-dilithiobithieno complex with TipB(OMe)2 affords a borole with an extended conjugated electron-rich π-electron system; the electronic perturbation by the introduction of push–pull substituents is described.

  3,3′-双锂代双噻吩复合物与TipB(OMe)2的反应生成了一种扩展共轭富电子π电子系统的硼杂环，本文描述了通过引入推-拉取代基对电子产生的扰动。
• The liquid crystal Click procedure for oligothiophene-tethered phthalocyanines – self-assembly, alignment and photocurrent
  作者：Moritz Dechant、Matthias Lehmann、Genya Uzurano、Akihiko Fujii、Masanori Ozaki

  DOI：10.1039/d1tc00710f

  日期：——

  A series of star-shaped liquid crystals (LCs) with a phthalocyanine donor core, oligothiophene antennae and fullerene acceptors have been successfully prepared. This hierarchical self-assembly results in a nanosegregated helical donor–acceptor–antennae LC-system promoted by the recently discovered Click procedure. This model system reveals all photophysical prerequisites for energy conversion, charge

  已经成功制备了一系列具有酞菁供体核，寡噻吩触角和富勒烯受体的星形液晶（LC）。这种分层的自组装导致了最近发现的Click程序促进了纳米级分离的螺旋形施主-受主-天线LC系统的发展。该模型系统揭示了能量转换，电荷产生和传输的所有光物理前提。可以通过棒涂生产150 nm的均匀非晶薄膜。退火不仅通过点击程序诱导了色谱柱的形成，而且使非澄清样品在夹心几何结构（ITO和Ag / MoO 3）。微观研究和光电流测量已证实了这一点，在退火步骤之后，光电流增加了300倍。